Characterization of four diol dehydrogenases for enantioselective synthesis of chiral vicinal diols

doi:10.1016/j.cjche.2021.05.019

Chinese Journal of Chemical Engineering ›› 2022, Vol. 47 ›› Issue (7): 145-154.DOI: 10.1016/j.cjche.2021.05.019

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Characterization of four diol dehydrogenases for enantioselective synthesis of chiral vicinal diols

Jiandong Zhang¹, Rui Dong¹, Xiaoxiao Yang¹, Lili Gao², Chaofeng Zhang¹, Fan Ren³, Jing Li¹, Honghong Chang¹

1. Department of Biological and Pharmaceutical Engineering, College of Biomedical Engineering, Taiyuan University of Technology, Taiyuan 030024, China;
2. Department of Environmental Engineering, Taiyuan University of Technology, Taiyuan 030024, China;
3. Shanxi Xuanran Pharmaceutical Technology Co, Ltd, Jinzhong 030600, China

Received:2021-01-16 Revised:2021-04-07 Online:2022-08-19 Published:2022-07-28
Contact: Jiandong Zhang,E-mail:zhangjiandong@tyut.edu.cn
Supported by:
This study was supported by the National Natural Science Foundation of China (Grant No. 21772141), the Shanxi Province Science Foundation for Youths (grant No. 201701D221042), the Key Research and Development (R & D) Project of Shanxi Province (201803D31050).

Characterization of four diol dehydrogenases for enantioselective synthesis of chiral vicinal diols

Jiandong Zhang¹, Rui Dong¹, Xiaoxiao Yang¹, Lili Gao², Chaofeng Zhang¹, Fan Ren³, Jing Li¹, Honghong Chang¹

1. Department of Biological and Pharmaceutical Engineering, College of Biomedical Engineering, Taiyuan University of Technology, Taiyuan 030024, China;
2. Department of Environmental Engineering, Taiyuan University of Technology, Taiyuan 030024, China;
3. Shanxi Xuanran Pharmaceutical Technology Co, Ltd, Jinzhong 030600, China

通讯作者: Jiandong Zhang,E-mail:zhangjiandong@tyut.edu.cn
基金资助:
This study was supported by the National Natural Science Foundation of China (Grant No. 21772141), the Shanxi Province Science Foundation for Youths (grant No. 201701D221042), the Key Research and Development (R & D) Project of Shanxi Province (201803D31050).

Abstract

Abstract: Enantiopure vicinal diols are important building blocks used in the synthesis of fine chemicals and pharmaceutical compounds. Diol dehydrogenase (DDH) mediated stereoselective oxidation of racemic vicinal is an efficient way to prepare enantiopure vicinal diols. In this study, four new bacterial DDHs (AnDDH from Anoxybacillus sp. P3H1B, HcDDH from Hazenella coriacea, GzDDH from Geobacillus zalihae and LwDDH from Leptotrichia wadei) were mined from the GenBank database and expressed in E. coli T7. The four DDHs were purified and biochemically characterized for oxidation activity toward (R)-1-phenyl-1,2-ethanediol, with the optimal reaction condition of pH9.0 (AnDDH), 10.0 (HcDDH) and 11.0 (GzDDH and LwDDH) and the temperatures at 40℃ (AnDDH), 50℃ (HcDDH) and 60℃ (GzDDH and LwDDH), respectively. The four enzymes were stable at the pH from 7.0 to 9.0 and below 40℃. Kinetic parameters of four DDHs showed that the HcDDH from Hazenella coriacea had high activity toward a broad range of vicinal diols. A series of racemic vicinal diols were successfully resolved by recombinant E. coli (HcDDH-NOX) resting cells co-expression of an NADH oxidase (NOX), affording (S)-diols and (1S, 2S)-trans-diols in ≥ 99% ee. The synthetic potential of HcDDH was proved by E. coli (HcDDH-NOX) via kinetic resolution of racemic trans-1,2-indandiol on a 100 ml scale reaction, (S, S)-trans-1,2-indandiol was prepared in 46.7% yield and >99% ee. In addition, asymmetric reduction of four α-hydroxy ketones (10-300 mmol·L^-1) by E. coli (HcDDH-GDH) resting cells resulted in >99% ee and 69-98% yields of (R)-vicinal diols. The current research expands the toolbox of DDHs to synthesize chiral vicinal diols and demonstrated that the mined HcDDH is a potential enzyme in the synthesis of a broad range of chiral vicinal diols.

Key words: Diol dehydrogenases, Kinetic resolution, Enantioselective, Chiral vicinal diols, α-Hydroxy ketone

摘要： Enantiopure vicinal diols are important building blocks used in the synthesis of fine chemicals and pharmaceutical compounds. Diol dehydrogenase (DDH) mediated stereoselective oxidation of racemic vicinal is an efficient way to prepare enantiopure vicinal diols. In this study, four new bacterial DDHs (AnDDH from Anoxybacillus sp. P3H1B, HcDDH from Hazenella coriacea, GzDDH from Geobacillus zalihae and LwDDH from Leptotrichia wadei) were mined from the GenBank database and expressed in E. coli T7. The four DDHs were purified and biochemically characterized for oxidation activity toward (R)-1-phenyl-1,2-ethanediol, with the optimal reaction condition of pH9.0 (AnDDH), 10.0 (HcDDH) and 11.0 (GzDDH and LwDDH) and the temperatures at 40℃ (AnDDH), 50℃ (HcDDH) and 60℃ (GzDDH and LwDDH), respectively. The four enzymes were stable at the pH from 7.0 to 9.0 and below 40℃. Kinetic parameters of four DDHs showed that the HcDDH from Hazenella coriacea had high activity toward a broad range of vicinal diols. A series of racemic vicinal diols were successfully resolved by recombinant E. coli (HcDDH-NOX) resting cells co-expression of an NADH oxidase (NOX), affording (S)-diols and (1S, 2S)-trans-diols in ≥ 99% ee. The synthetic potential of HcDDH was proved by E. coli (HcDDH-NOX) via kinetic resolution of racemic trans-1,2-indandiol on a 100 ml scale reaction, (S, S)-trans-1,2-indandiol was prepared in 46.7% yield and >99% ee. In addition, asymmetric reduction of four α-hydroxy ketones (10-300 mmol·L^-1) by E. coli (HcDDH-GDH) resting cells resulted in >99% ee and 69-98% yields of (R)-vicinal diols. The current research expands the toolbox of DDHs to synthesize chiral vicinal diols and demonstrated that the mined HcDDH is a potential enzyme in the synthesis of a broad range of chiral vicinal diols.

关键词: Diol dehydrogenases, Kinetic resolution, Enantioselective, Chiral vicinal diols, α-Hydroxy ketone

Jiandong Zhang, Rui Dong, Xiaoxiao Yang, Lili Gao, Chaofeng Zhang, Fan Ren, Jing Li, Honghong Chang. Characterization of four diol dehydrogenases for enantioselective synthesis of chiral vicinal diols[J]. Chinese Journal of Chemical Engineering, 2022, 47(7): 145-154.

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Characterization of four diol dehydrogenases for enantioselective synthesis of chiral vicinal diols

Characterization of four diol dehydrogenases for enantioselective synthesis of chiral vicinal diols

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